1 research outputs found
Chemoselective Synthesis of 3‑Bromomethyloxindoles via Visible-Light-Induced Radical Cascade Bromocyclization of Alkenes
A novel
visible-light-induced radical cascade bromocyclization
of N-arylacrylamides has been accomplished. This
reaction overcomes the overbromination at the benzene rings suffered
in traditional electrophilic reactions, thus enabling the first highly
chemoselective synthesis of valuable 3-bromomethyloxindoles. The combination
of pyridine and anhydrous medium is identified as the key factor for
the high chemoselectivity in the current photoreaction system, which
might work by suppressing the in situ generation
of low-concentration Br2 from N-bromosuccinimide.
Moreover, the mild reaction conditions ensure the generation of a
wide range of the new desired products with excellent functional group
tolerance